Resolution of 4-Hydroxy-2-cyclopentenone Derivatives by HPLC on Cellulose Triphenylcarbamate Derivatives

Abstract

Trialkylsilyl ethers of 4-hydroxy-2-cyclopentenone, which are the key compounds for the syntheses of prostaglandins, were completely resolved on chiral HPLC columns packed with cellulose triphenylcarbamate derivatives.

Synthesis of Chiral Cyclopentenones

“…Preparative chiral HPLC has been typically used to provide samples for characterization and biological testing. A few methods have been reported for the resolution of 4-hydroxycyclopentenone derivatives using cellulose carbamates, benzoates, and acetates as stationary phases. − Curiously, Loža et al reported enantiomeric enrichment of certain racemates after achiral column chromatography purification. Accordingly, partially resolved 4-hydroxy-2-carboxymethylcyclopentanes and two (−)-5-oxa-6-oxoprostaglandin E 1 C(15) epimers, synthesized from partially enantiomerically enriched (∼40% ee) 4-hydroxy-cyclopentenones, displayed surprising behavior during achiral column chromatography purification.…”

Novel γ-Aminobutyric Acid ρ1Receptor Antagonists; Synthesis, Pharmacological Activity and Structure−Activity Relationships

“…To access this intermediate, initially (±)-4-hydroxycyclopent-2-en-1-one ( 7 , Scheme ) was synthesized from 2-methyl furan as described by An et al Several enantioselective methods exist for the production of the individual enantiomers of 4-hydroxycyclopent-2-en-1-one ( 8 and 9 , Scheme ), due to its extensive use as a synthon in prostaglandin chemistry . These include enzymatic, chromatographic, and synthetic procedures. – The method of Khanapure et al using l -tartaric acid as the source of chirality was selected due to the extremely high reported enantiomeric excess (e.e.) and the potential for multigram scale preparation.…”

Discriminação quiral por CLAE em carbamatos de polissacarídeos: desenvolvimento, aplicações e perspectivas

“…Uma das características importantes destas fases estacionárias quirais (FEQs) é que elas têm sido úteis na resolução de uma grande variedade de compostos, incluindo os alifáticos. A presença de grupos aromáticos, embora facilite a resolução, não tem sido, neste caso, essencial 2,53 , como pode ser exemplificado pelas discriminações quirais obtidas para derivados de αpineno 54 , derivados da 4-hidróxi-2-ciclopentanona 22,55 , ciclobutanonas 56 , β-lactamas 57 , e prostaglandinas 58 .…”